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有机化学 ›› 2007, Vol. 27 ›› Issue (12): 1542-1546. 上一篇    下一篇

研究论文

1-芳甲基-3-芳基吡唑-5-羧酸乙酯衍生物的合成与生物活性评价

丁晓玲a,b，孟宁c，夏永a，王丽娟a,d，张晓峰a
赵宝祥*,a，苗俊英*,c   

  1. (a山东大学化学与化工学院有机化学研究所 济南 250100)
    (b青岛大学高等职业技术学院 青岛 266061)
    (c山东大学生命科学学院发育生物学研究所 济南 250100)
    (d青岛帝科精细化学有限公司 青岛 266101)
  • 收稿日期:2007-01-15 修回日期:2007-05-20 发布日期:2007-12-04
  • 通讯作者: 赵宝祥,苗俊英

Synthesis and Bioactivity Evaluation of Ethyl 1-Arylmethyl-3-aryl-1H-pyrazole-5-carboxylate Deriva-tives

DING Xiao-Linga,b, MENG Ningc, XIA Yonga, WANG Li-Juana,d
ZHANG Xiao-Fenga, ZHAO Bao-Xiang*,a, MIAO Jun-Ying*,c   

  1. (a School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100)
    (b College of Advanced Professional Technology, Qingdao University, Qingdao 266061)
    (c Institute of Developmental Biology, School of Life Sci-ence, Shandong University, Jinan 250100)
    (d Qingdao DIC Finechemicals Co. Ltd., Qingdao 266101)
  • Received:2007-01-15 Revised:2007-05-20 Published:2007-12-04
  • Contact: ZHAO Bao-Xiang, MIAO Jun-Ying

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在碳酸钾存在下, 以丙酮或乙腈为溶剂, 3-芳基吡唑-5-羧酸乙酯与芳甲基氯发生亲核取代反应, 以较好收率得到1-芳甲基-3-芳基吡唑-5-羧酸乙酯衍生物. 取代基以及溶剂对反应收率有较大影响. 1H NMR, 13C NMR, IR和MS表征了化合物的结构. 通过X射线衍射分析测定了化合物3c的晶体结构. 所得化合物3a～3d在5～20 μmol•L－1浓度范围对血管内皮细胞(HUVEC)凋亡具有促进活性, 其效果具有浓度依赖性.

关键词: 吡唑衍生物, 合成, 结构表征, 凋亡, 内皮细胞

Ethyl 3-aryl-1H-pyrazole-5-carboxylate reacted with arylmethyl chloride in acetone or acetonitrile in the presence of potassium carbonate to afford 1-arylmethyl-3-aryl-1H-pyrazole-5-carboxylate derivatives in good yields. The substituent on aryl moiety and solvent can influence on the yields of the reactions. The structures of all products were confirmed by 1H NMR, 13C NMR, IR and MS spectra. The structure of compound 3c was determined by X-ray single crystal diffraction method. The compounds 3a～3d promoted HUVEC apoptosis at the concentrations of 5～20 μmol•L－1 to a certain extent and the effect on the cell viability was dose-dependent.

Key words: synthesis, characterization, apoptosis, vascular endothelial cell, pyrazole derivative